


Since We've No Place to Go

by pinkevilbob



Category: Critical Role (Web Series)
Genre: Alternate Universe, F/M, Prompt Fill
Language: English
Status: Completed
Published: 2020-03-18
Updated: 2020-04-27
Packaged: 2021-03-01 00:34:21
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 5,818
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23206318
Author URL: https://archiveofourown.org/users/pinkevilbob/pseuds/pinkevilbob
Summary: I'm filling prompts since we're all cooped up and it's been a rough week.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 58
Kudos: 107





	1. Chapter 1

**Author's Note:**

> Okay so Funnygirlthatbelle requested 'baking', and this just popped into my head.

The only light in Caleb's apartment for the last three days was the glow of his computer screen. It had been a bad week, but the same could be said about most of his weeks. This week in particular had been rough though. Nott, or rather Veth, had moved out to be with her husband and son which Caleb would never blame her for. In fact, he was proud of Veth, but it left him all alone except for Frumpkin. Except that Frumpkin had gotten sick and was at the vet. The cat was okay now, but the vet wanted to observe him for another night to make sure that he was okay. So Caleb was completely alone.

Caleb had been alone for years, so it shouldn't bother him, but he had grown accustomed to company now. Which was probably why he had fallen down the rabbit hole of watching cooking videos. There was something soothing about them. They almost made him feel like there was someone else in his empty apartment.

The best one he'd found was a baking channel. Hosted by bubbly tiefling called Jester, it would always raise up his spirits. Everything looked delicious, but it was Jester herself that always had Caleb clicking immediately on her next video. She was quick with a smile and faster with a dirty joke. For the first time in years, Caleb found himself laughing.

That night Jester was doing her first baking live stream and Caleb was glued to the screen watching it. He had chat up to keep up with the ingredients and measurements(not that he'd ever make anything from the show. He had the cooking skills of a shoe, which was to say absolutely none).

"Alright everyone, our blueberry cobbler is nearly done!" Jester said. The plump(and adorable) baker clapped her hands together, but there was something about her that felt off. She'd kept looking off screen and Caleb could've sworn she was fighting a frown. But what did he know? Caleb didn't actually know her, he just liked her videos.

Her timer buzzed and Jester opened her oven. "Omigosh guys, I wish that you were all here to smell how tasty this is!" Jester pulled out the cobbler and took a big sniff, her tail wagging behind her. "I can't wait to taste thi-" She started to go to the counter, but she nearly tripped and dropped her cobbler. 

Caleb winced at the crashing sound and his fingers began typing in the chat before he could stop himself. "Are you okay?" His stomach dropped when he read the rest of the chat with their 'lol's and 'FAIL's.

Jester stood there for a moment staring at her tablet and the chat. She blinked rapidly.

"It looked good," Caleb typed. "I'd still eat it off the ground." He'd eaten far more questionable things living with Nott.

The baker giggled. "Frumpkin_fan! You can't eat floor cobbler! It has glass in it." She cleaned up the cobbler as teased Caleb about wanting to still eat it, but Jester was smiling again.

"Still better than anything I could make," Caleb typed back. "I burn everything."

"But anyone can bake," Jester said. "It's super fun and relaxing. You just need to find the right recipe for you." She hummed tapping her chin. "Oh! I know just the one." Jester ran over to her cupboard and pulled out ingredients. "This is the tastiest thing ever. Mug cake! You make it in the microwave, so you can't burn it! Now I expect you to follow along, Frumpkin_fan, and I want to see how tasty yours are when we're all done."

Caleb stared at the screen sitting on his couch. She didn't really expect him to cook along with her, did she? But he found himself turning on the light for the first time in days and taking his laptop to the kitchen. "Ready to start."


	2. Chapter 2

**Notes for the Chapter:**

> Anon requested a fic of Jester finding a lost Frumpkin. So here it is.

Caleb searched the house high and low. Every box was opened, moved, and set back into place. Each cupboard was carefully inspected. But he could find neither hide nor hair of Frumpkin. 

He liked to think of himself as a good cat owner. Caleb kept Frumpkin inside where he was safe and made sure that Frumpkin got enough play time and plenty to eat. But somehow Frumpkin had gone completely missing.

A hole was nearly worn into the floor with Caleb's pacing. His phone rang, but it was a number he wasn't familiar with, so he didn’t bother answering it. “Where could he be?” Caleb muttered to himself. His phone buzzed at him. Whoever called him left a message. With a sigh, Caleb hit play.

“Hi, so um, I found Frumpkin outside and he’s super cute and sweet and I’m betting you want him home. So give me a call and I’ll bring him right over. Doot doot doot doot doo! Bye!” 

Caleb stared at his phone and had to fight back a laugh. It was the strangest and oddly enough sweetest phone messages he’d ever gotten. He called the number back already heading out the door. 

“Hello?”

“Ja, hello, this is Frumpkin’s owner. Is he still with you?” Caleb asked.

“Yep! I got the little lovemuffin right here!” It was a feminine voice with an accent that Caleb couldn’t quite place.

Caleb smiled with a sigh. “Good. I can meet you right away. Where are you?”

“Oh, I’m at right by the Chasisty’s Nook.”

“I’m on my way.” Caleb ran the whole way to their smut shop(he was never the athletic sort, but Frumpkin was worth running for). When Caleb saw the woman holding Fumpkin his heart fluttered both at the sight of his cat and a little bit because the woman was cute. The cat leapt out of her arms and ran right to Caleb. “There you are,” Caleb said scooping Frumpkin up.

“You must be Frumpkin’s owner.” Her hair was blue and she grinned up at Caleb.

He nodded. “Ja, I am. Thank you for finding him.”

“No problem. He was super cute, and I saw his collar so I figured I’d call the number. I’m Jester.” She extended her hand towards him.

Caleb adjusted Frumpkin in his arms and took her hand. “Caleb. Caleb Widogast. I was so worried about him.”

Jester smiled at him. “Then I’m super glad that I found him.”

“Is there anything I can do to repay you?” Caleb asked. “Coffee perhaps?” He couldn’t quite afford it, but he did owe Jester and she was very cute.

“Can we go somewhere we can bring Frumpkin? I wasn’t done petting him yet.”

Caleb nodded. “There’s always my place. Frumpkin’s always invited there.” And the coffee was free there.

“Great!” Jester’s grin widened. “It’s a date!”

His heart fluttered even heart. If Jester kept being so cute, he was going to need a pace maker.


	3. Chapter 3

**Notes for the Chapter:**

> Another anon asked for "she takes the traveler up on his offer to explore the different planes and Caleb’s reaction?" Which was a tasty prompt.

Jester stared down at her skirt fiddling with the pleats. "So, I talked to the Traveler."

"Ja?" Caleb sat next to her. He had been reading, but he'd closed his book as soon as Jester spoke.

"He wants to take me to other planes. As soon as next week," Jester said.

Caleb hummed thoughtfully. "And what did you say?"

She sunk down lower in her seat. "Yes." Jester closed her eyes and braced herself for his response. But there was none. Cautiously she opened her eyes. 

He was playing with his lucky rock, rolling it over and over in his hand. Caleb didn't seem happy, but he wasn't mad at her either, which she was afraid of.

"Well, aren't you going to say something?" Jester asked.

Caleb sighed. "I wish you the best of luck."

"You're not upset?" Jester had been worried to tell her friends her plans in fear of their reactions.

"Nein. Why would I be? You've been offered a grand opportunity," he said.

Jester turned to face him. "But don't you think I'm being silly or dumb running off like this?"

He shook his head. "Why would I? Jester, you're an incredible woman who's full of wisdom and charm. I trust your decisions."

"Really?" No one had ever told her that before.

"Ja. I really do," Caleb said softly.

Jester relaxed for the first time since she agreed to go with the Traveler. "So you think this is a good idea?"

"Well, you trust the Traveler and I trust you, so ja, I suppose I do." Caleb frowned a little though. "Tell me, will you return? You can't stay away forever."

Jester breath caught in her throat. "I can't?"

"Nein, you can't. Your mother, you'll miss her, ja? Surely the Traveler will let you visit her."

She deflated a little surprised at her own disappointment. Did she want Caleb to say something different? "He didn't say how long we'll be gone, but he knows how much my mom needs me. And I'll probably miss her like crazy. I'll come back someday."

Caleb nodded. "Good. We'll miss you too. You're very special. I don't think we could've done half the things we've done without you."

"You really think so?"

"I know so. We would've lost Caduceus long ago if it weren't for you and the Traveler," Caleb said. "And, even if you hadn't, you've done more miracles with your smile than even I can count." 

A warmth grew in Jester's chest. "Thank you."

"It's I who should be thanking you," Caleb said. His face glowed a little read. "Jester, may I be forward and ask a request to you?"

"Sure."

Caleb took a deep breath. "One day, when you've decided that you're done with your journeying with the Traveler, please, return to us. But only when you know that you're ready. Let no one decide that for you."

Jester stared at Caleb, tears welling in her eyes. "Yeah, I promise. I'll come back. When I'm ready."

He grinned showing off his dimples. "Danke."


	4. Chapter 4

**Notes for the Chapter:**

> From Anon: "If you’re still taking prompts - what about classic College/University!AU where both Caleb & Jester are students of different subjects/majors? And if you want more details (obv it’s your fic and you can take it where u want) - maybe it’s spring break but they’re both staying in town and somehow they meet (in a library? Coffeshop? Campus? your choice :) Thank you and have a good day!"
> 
> So I went with a stuck in spring break college AU. I hope you all like it!

Jester fought back the tears. She was not going to cry. All crying did was make people around her sad too. But it was hard not to cry when it was spring break, she was stuck on campus do to an emergency back at the Lavish Chateau(her mom was okay though), and she couldn't go home to visit her mom. Just thinking about made fat tears well up in her eyes. Shaking her head, she denied the tears escape. This was going to be the best spring break ever anyways.

There was plenty she could do; hang out with her roommate Beau, flirt with Fjord, and the Traveler was always down for making some mischief. Jester was going to make it the best spring break ever.

* * *

  
It was official. This was going to be the worst spring break ever. Beau was going on a training camp thing with Dairon, Fjord had signed up to spend the whole break on a fishing boat, and the Traveler was called away on business. Leaving Jester all alone for an entire week.

She hadn't even wanted to go to college in the first place. The only reason she agreed to going was so she didn't disappoint her mom. And now Jester was all alone. All Jester wanted to do was flop down on her bed and cry, but Beau was packing in their dorm room and the last thing Jester want to was damper Beau's spirits.

So Jester found herself walking in a loop on campus trying to convince herself that it really wasn't so bad, which was easier said than done. She wasn't looking where she was going just focusing on her feet and not crying, and she ran right into someone and fell down on the ground. And that was it, the straw that broke the camel's back.

Big fat tears began to roll down Jester's face. All of her shook with heaving sobs. "Oh no," Jester said struggling to wipe her face dry.

"Are you alright? I didn't hurt you did I?"A scrawny red headed man knelt before her. He was dirty and wore a shabby, brown coat.

"Yeah, I'm fine," Jester said between sobs. "I'm totally okay. You don't have to worry about me."

He stared at her. "Are you sure?"

Jester nodded wiping away tears that were quickly replaced. "Yep." She gasped for breath. "Just fine."

"Okay." He reached into his pocket and pulled out a small cat. "Will this help? Not that you need any help."

Her jaw dropped at the cat, which was absolutely adorable. "Yes. Not that I need any." Jester delicately took the cat. It purred in her hands.

"His name is Frumpkin."

"Hi Frumpkin, I'm Jester," she said. Jester looked up from the cat. "What's your name?"

The man blushed and ducked his head down a little. "Caleb. Caleb Widogast."

"It's nice to meet you, Caleb."

"Ja, it's nice to meet you too." Caleb scratched Frumpkin behind his ear. "Are you feeling better?"

Jester nodded. She was still sniffling, but her tears had stopped. "Yeah."

"I'm sorry if I hurt you," he said

"Oh no, it wasn't your fault at all." Jester sighed. "It's just that spring break's next week and I'm stuck here while all my friends run off having fun." She knew she wasn't being fair to her friends, but this wasn't fun to her either. "I can't even visit my mom."

Caleb hummed a little and nodded. "Frumpkin and I have to stay here too, and our friend's off visiting her family. I, I think Frumpkin's going to be lonely this week, so maybe you can visit him?"

Jester stared at him. "Really?"

"Ja. Frumpkin seems to really like you." As if on cue, Frumpkin purred in her hands.

"I super like you too, Frumpkin," Jester said. "And you won't mind?"

Caleb shook his head. "Nein, I'd be delighted to share your company. With Frumpkin of course."

"Of course." Jester giggled. "Thank you Caleb." Maybe this spring break wouldn't be so bad after all.


	5. Chapter 5

**Notes for the Chapter:**

> So funnygirlthatbelle and rose-lattes made a little list of widojest prompts for the current hiatus, so I decided to write a little something for the prompt ‘books/in the library’. And by little something, I mean HOGWARTS AU!

The best time for reading in the Hogwarts library Caleb had found was after hours. There were no other students around, so for once, it was blissfully quiet. To be fair, he wasn't supposed to be there either, and if Caleb got caught, he'd get detention for sure. But for the few hours to read by himself, it was worth the risk.

He was halfway through a tome on transfiguration when a sound interrupted his reading. It was a soft thump like a book being dropped. Caleb froze; he wasn't alone after all. Ducking under the table, he waited with bated breath.

"S%*$!" a young voice shouted.

Caleb poked his head out. That didn't sound like the librarian, Zeenoth. It was most likely just a student, but Caleb had never encountered another student before on his night time visits(sure Nott would come along sometimes, but she was currently serving detention for blowing up the potions classroom). He crept out to the shelves and discovered a Hufflepuff girl standing there. She was a bit shorter than Caleb and blue with a tail and horns. There were a few tiefling students at Hogwarts, but most of them were a different type of trouble than the kind Caleb was up to so he made a point to avoid them.

The tiefling girl gasped. "Oh crap! I'm caught!" She cast a spell and then there were two of her and one of them scampered off.

"Not really. I'm not supposed to be here either," Caleb said.

"Oh," the tiefling girl said. She almost sounded disappointed. "You sneaked out to be here too?"

Caleb nodded. "Ja, it's quieter than the common room and there’s more books."

"That's boring."

He huffed. "And what you're up to is more interesting?"

"Yep!" She beamed at him. "I'm turning all the books around so no one knows which one's which."

"You got me there, that's more interesting." Nott would probably like this strange Hufflepuff. "But why?"

She pouted. "That should be obvious."

Caleb stared at her. "It should?"

"Yep! See when people come in tomorrow they'll all be 'oh no, I can't find the book on smiling charms I needed for charms class!' and it'll be hilarious," she said.

He reached over her head and hovered a moment before grabbing the fourth book from the left. "Here."

"You remembered just where it was?" The tiefling's eyes grew wide.

Caleb blushed. "It's not that impressive. I just have a good memory and go in here a lot."

The tiefling shook her head. "No, that's super impressive. Hi! I'm Jester." She stuck out her hand.

"Caleb, Caleb Widogast," he said, shaking her hand. "You're not going to be able to flip all these books by yourself."

"Are you offering to help, Caleb?" she asked with a wide grin.

He gave it a thought. "Ja, I suppose I am." Caleb took out his wand and flicked it casting a haste spell on her.

Jester looked confused for a moment before her smile grew even bigger and she got to work turning the books around. She moved so fast Caleb could barely follow her.

With a chuckle, Caleb began to slowly and carefully turning books around at the other end of the library.

"Done!" Jester declared a couple of minutes later meeting up with Caleb.

"Congratulations," Caleb said.

Jester nodded. "Yep! And it's all thanks to you!" She stood up on her tiptoes and kissed Caleb on the cheek. "We should probably sneak out now."

A hot red blush covered Caleb's face. "J-ja." He stood stock still.

"That means we should leave, Cay-leb," Jester said. She grabbed his hands and gave them a little tug.

He followed her numbly.

"You're a Ravenclaw, right? Fourth year?" Jester asked.

Caleb finally shook away his fog. "Uh, ja. Ja I am."

Jester led the way down the halls still holding Caleb's hand. "I'm in the third year! So we don't have any classes together."

"Nein, we don't."

"It would be a lot of fun if we did though," Jester said. "We should totally hang out more."

He could feel his blush returning. "Really? You think so?"

"Well yeah. You're super clever and it was a lot of fun pranking the library together," Jester said. "I know! We should have breakfast together tomorrow. My year mates are super boring."

"I would like that very much," Caleb said. 

Jester suddenly stopped and Caleb realized that they were in front of the Ravenclaw Tower. "Here we are! Your home."

Caleb almost blurted out that he had no home, but instead he nodded. "Ja, danke."

"You're welcome." Jester beamed at him. "Ok, so I should be sneaking back to my room now, but you have a goodnight Caleb." She waved him goodbye, spun around, and skipped away.

He stood there waving for a long moment. Caleb wasn't sure he knew what just happened, but he liked it.

**Notes for the Chapter:**

> Liam says that Caleb is Ravenclaw and honestly that makes a lot of sense to me. I went with Hufflepuff for Jester because I feel like she's very loyal and a little bit because I don't know if she'd fit in the other houses. Like yeah she's got some of the other qualities, but I don't think she'd fit in their cultures if that makes sense.


	6. Chapter 6

**Notes for the Chapter:**

> Okay so from this week's prompts, I chose Stargazing and well, I kinda got carried away. Hope you all like it!

The thing about stars was that even when you couldn't see them they were there. No matter how bright it was or how many clouds were in the sky, the stars were out there. Jester liked how they were like the Traveler that way. When she was little, she'd make up little stories about them, and then when she grew older, she'd track them and draw them on her ceiling. What she wanted more than anything though was to see a star in person. Her mother told her that the stars were too far to visit and that she would miss her little saphire if she were to go. Which was true, but then Jester learned that it was also impossible to to visit the stars. So she waited for one to come to her.

After years of tracking the stars, her efforts finally paid off. A star was falling, and if Jester was right, it would land right outside of Nicodranas. Grabbing a jar and a shovel, Jester ran outside. This was a once in a lifetime opportunity and Jester wasn't going to let it pass her by. It was growing light out by the time Jester reached her destination, a small beach. Rocks made it tricky to get to, but Jester wasn't going to let that stop her.

A crater sat in the sand and Jester could hardly believe her luck. She knew that she knew what she was doing, but an ugly doubt had been poking at the back of her head. Cautiously, Jester approached the rater. Despite all her day dreaming, Jester didn't know what a star would look like. Jester poke her head over the edge of the crater and frowned. In the middle of the crater sat a naked man. He wasn’t ugly or anything, in fact, he was quite handsome with a good chin and reddish brown hair, but he was not a star. "What are you doing here?" she asked.

"I fell," The man said. His voice was vaguely monotone and he stared upwards.

"Ah, do you need help up?" Jester asked.

He looked at her and Jester gasped at the intensity of his blue eyes. There was a glow to them that Jester never imagined being possible. “Could you?”

Jester nodded. “Yep! I’ll get you out of here in no time.” She scrambled down the crater and nearly tripped once she got to the bottom. He steadied her and Jester noticed just how naked he was. Hurriedly, Jester took off her coat and handed it to him.

The man stared at the coat turning it over and over in his hands until Jester helped him put it on. It was short on him, but it was more than wide enough to cover everything. He stared at the sleeve that didn’t quite cover his arm. “Danke.”

“You’re welcome,” Jester said. “I’m Jester!” She held out her hand to shake.

He gently took her hand, turning it around examining it. Jester wrinkled her nose. "You're weird."

"I'm Bren," he said without looking up from her hand.

"So why were you out here?" Jester asked.

He looked up with his piercing blue eyes. Jester could've swore that they glowed, but that wasn't possible. "I told you, I fell."

"Well, yeah that's why you're in the hole, but why were you out on the beach at night?"

"I fell," he said again. “I should be going. I’m sorry to trouble you.” Bren turned away towards the earth wall of the crater and immediately tripped.

Jester caught him. “Careful, it’s super slippery here.”

Bren nodded and stepped away from her. “I’ll keep that in mind.”

“Wait!” Jester called out remembering why she’d come there in the first place. “Have you seen a star? One fell and it should’ve landed here.”

Freezing for a moment, Bren turned away shaking his head. “Nein, I can’t say that I’ve seen a star here.” He began to try to climb out of the crater and nearly immediately he fell backwards.

“Bren!” Jester cried.

A bright light suddenly burst out of Bren nearly blinding Jester. She instinctively threw up her arms blocking the light. Bren said something loudly that could only be a curse even if Jester didn’t recognize the language. The light dimmed, but Bren was still vaguely glowing.

Jester stared at him stunned by what just happened. “Are you okay?” she asked, unable to separate the hundreds of questions running through her head.

“I will be,” Bren said with a deep frown. “Just when I finally turned my shine off.”

“What just happened?”

Bren rubbed his arm. “I may have lied to you about not seeing a star here.”

“Did it hit you? Are you sure you’re okay?” Jester asked.

“Nein, I’m fine. Nothing hit me but the ground.”

Jester tilted her head. “The ground?”

“I’m the star you were looking for.” Bren looked away the glow on his face turning red.

Her jaw dropped. “You’re a star?”

He nodded. “Ja, I am.”

“I’ve always wanted to see one! I’m so glad to meet you!” Jester grabbed both of his hands. Bren stared at her and she dropped them. “Sorry, this is just super exciting.”

“I’m not that special. There’s thousands of us,” he said looking up at the sky.

Jester shrugged. “Yeah, but you’re the first that I’ve met, so you’re special to me, Bren.”

The glow around Bren burned brighter again. He scowled at this. “Stop saying my name. It looks like my shine is less under my control than I had hoped it would be. I’ll need to come up with something else.”

“Caleb’s a good name,” Jester suggested.

“Caleb,” he said, testing it. “It will do, danke.” The star looked up at the edge of the crater.

Jester stood next to him. “Caleb.” He remained at the same amount of light. “Do you have a way back to the sky? Or like a place to go here?”

Caleb shook his head. “Nein, but I will figure something out.”

“You can come home with me,” Jester said, not daring to look at him. “There’s a lot of rooms at the Lavish Chateau. You can stay there.”

A frown crossed Caleb’s face. “I don't know.”

“Why not? My mom basically runs the place and you can be safe there,” Jester said.

“Safe,” he repeated.

Jester nodded. “Yeah, and we can have so much fun together and I can teach you so much about Exandria and stuff!”

Caleb grinned slightly, but it just highlighted how sad his face’s default was. “I do like to learn.”

“That settles it then! You’ll stay with me!”

“For now,” Caleb said. “A star is not a safe thing to keep.”

A frown tugged at Jester’s face. “Is a star a safe thing to be?”

His face went blank. “That’s not for you to worry about.”

Jester glared at that phrase. Most things in life weren't for Jester to worry about. “Do you know why you fell then?”

“It’s,” he took a deep breath, “a complicated story.”

“Well, since you’ll be staying with us, you’ll have a lot of time to tell it then,” Jester said. “I’m a super good listener.”

Caleb looked at her and almost grinned. “Perhaps I will one day, but not tonight.”

“What do you want to do tonight instead?” Jester asked.

“I don’t know. I’ve never been on Exandria before. Never had a body before either actually.”

Jester clapped her hands. “Oh my gosh, Cay-leb. You are in for such a treat. I’ll show you all the tasty things and all the coolest things there are in Nicodranas.”

He smiled for once. “I look forward to it.”


	7. Chapter 7

**Notes for the Chapter:**

> A super short one, but I hope that's okay. This was requested by laylia who won a little drawing in the widojest discord.

Jester happily swung her feet back and forth as she sent her third Sending. "You should've seen him mom. He was very brave and noble. And then he got me some pastries. So it was a super good day."

Marion chuckled. "This is the fourth time you Sent me and only talked about Caleb. If I didn't know better I'd say you fancied him."

"What?" Jester said out loud to no one. It wasn't like that at all. Caleb was just the most interesting lately. For the last week and a half. So it really didn't mean anything. Jester rolled her eyes and prepared another sending. "It's not like that at all Mom. Caleb's just sweet, handsome, can be funny, has a nice chin, and is always willing to listen to me. Oh, and when he says my name it's super cute and-" She stopped partially because she'd ran out of words a while ago and partly because her mom may have had a point.

"Oh, well if that's all it is then. That's all it is." Even unseen, Marion's smile could be heard. "I hope you're doing well and know that I send you my love."

Jester sat still with a frown. "Mom? How did you know that you were in love?" For once, Jester didn't pad out the message.

"Hmm, that's a tricky question. I suppose I just knew by the way just thinking about him made me smile. Hope that helps," Marion said.

"Yeah, it does," Jester said to no one. She sunk down in her a chair with a sigh. "Maybe I am in love. A little bit." A grin spread across her face. Maybe being a little bit in love with Caleb wouldn't be so bad.


	8. Chapter 8

**Notes for the Chapter:**

> Oftennot requested awkward lovestruck teens on their first date. This ended up going in a different direction that I had originally intended, but I hope it still counts.

A baker's dozen of dresses were scattered all over the floor. "I've got nothing to wear!" Jester flopped backwards onto her bed melodramatically.

"Absolutely nothing," the Traveler said with a smirk.

"I know," Jester said, sitting up. "And my date is in 15 minutes. This is a disaster."

The Traveler picked up a dress and looked over. "Which one is this with? The green mama's boy?"

"Fjord?" Jester shook her head. "Nah, it's Caleb."

"Hmm, I like the looks of that one, but he has no reckoning for fashion. You could wear a flour bag and he'd still kiss your feet," the Traveler said.

Jester giggled. "He really wouldn't."

The Traveler tapped his chin. "I'd think you'd be surprised. Even in your ugliest frock, he can't keep his eyes off of you."

"Really?"

"Really. Wear what you like and stop trying to please him," the Traveler said. "Besides, he's just a teenage boy. Their opinions count for nothing."

Jester rolled her eyes, but she picked up her favorite pink dress.

* * *

"This was a terrible idea," Caleb said for the 14th time. "What was I thinking?"

"That it would be fun to spend an evening with Jester?" Nott didn't even look up from her button collection.

Caleb straightened his shirt for the 18th time. "Are you sure I look okay? Maybe I should change."

Nott rolled her eyes. "You already changed twice." Actually, he’d changed three times, but he wasn’t going to correct Nott.

"Right. Right." Caleb paced the floor. This was happening. He was actually going on a date with Jester. It was a dream come true, but now that it was nearly time, Caleb was nervous more than anything else. "Maybe this is a mistake. Maybe Jester didn't mean to say yes."

"And maybe she did. You're a handsome young man and any girl would be happy to date you," Nott said.

Caleb sighed. "I think you're grossly mistaken."

"Give her a chance," Nott said. "She seemed excited to me for the date."

"I guess. Thanks."

Nott waved him off. "It's nothing. Now go change. Your first shirt was much better."


	9. Chapter 9

**Notes for the Chapter:**

> The prompt last week was tattoo.

The bell jingled over the door as a man came into the tattoo parlor. Jester couldn't help but raise an eyebrow at him. He looked like he should be in a bookstore and not a tattoo shop. "How can I help you?" Jester asked brightly.

"Oh, ja, I have an appointment?" he said, sounding a little apprehensive.

"Caleb, right?" Jester asked. He had called in a few days before and explained what he wanted. It was a simple design, but a fun one to make. A little stylized cat on a book.

He nodded. "Ja, that's me. Is now a good time? I could come back later if you'd like."

Jester shook her head. "No, you're just in time." Never mind the fact that it was the most boring afternoon ever at the tattoo shop.

"Ah good," he said, but he looked almost disappointed.

"Did you like the design I sent you?" Jester asked.

Caleb nodded and he actually looked excited. "Ja, it's a very good design."

"Great!" Jester grinned widely at him. "So, where do you want your tattoo?"

He paled a little, but he rubbed his left bicep. "Right here. It'll be easy to cover."

Jester frowned a little. "Do you work at a place that doesn't allow tattoos or something? I'd never be able to handle that sort of thing."

"It's not quite that they don't allow tattoos at the library. I just don't want people to see it," Caleb said.

"That's fair. Tattoos mean different things for different people." Jester led him to the tattoo chair. "Have you ever gotten a tattoo before?"

Caleb swallowed. "Ja, I have. That was years ago though. Over a decade and a half."

"Can I see it? Or is it like on your butt?"

He turned bright red. "Nein, it is on my other shoulder." Caleb stiffly removed his coat and then his shirt. His skin was pale as alabaster. The tattoo on his arm had faded some, but Jester could still tell that it was for some university.

Jester smiled. "Looks like you hold colors great. Are you ready for me to get started?"

"Nein, but I will not be more ready than this," Caleb said.

"Do you really want this tattoo?" Jester asked as she prepped his arm.

Caleb shook his head. "I lost a bet, but this isn't so bad. They let me actually choose what I'm getting."

Jester bit her lip. She'd seen bets resulting in tattoos, but she'd never had a client look so uncomfortable at the pretense of getting a tattoo. "Are you sure you want this?"

"The punishment game will be worse," he said, wincing at the thought of it.

"If you say so." Jester grabbed her tattoo gun and pressed it against Caleb's arm. 

He flinched away violently, pulling away his arm. “Sorry, I wasn’t ready.” Caleb seemed ashamed.

“A lot of people are nervous their first time or even their second,” Jester said. “Tell you what? I’ll count down for you this time. Does that sound good?”

“Ja, that sounds great,” Caleb said.

“Great!” Jester said, smiling at him. “Alright, one two three.” She started the first line of the tattoo.

Caleb gripped the arms of the chair so tightly Jester almost thought he would break it.

She watched him for a long moment not continuing the tattoo. “Caleb? Are you afraid of needles?”

“Ja, but only a little,” Caleb said, not looking at Jester. “You can keep going.”

Jester set her tattoo down and leaned forward. “Did your bet say how big your tattoo had to be?”

“Nein, not really,” Caleb said.

“Well then, your tattoo’s done.” Jester held up a mirror for him to see it in.

Caleb frowned. “You can barely see it.”

“But it’s still a tattoo.”

“Ja, it certainly is,” Caleb said a smile slowly creeping over his face. “It might be enough to satisfy the terms of the bet, but I don’t want to waste your time or your design.”

Jester tapped her chin and then jumped up. “Oh! I have the best idea! Just wait a moment!” She ran over to the storage closet and pulled out a henna kit. “This doesn’t take any needles at all and it’s still a tattoo. Unless you think it’s dumb.”

Caleb shook his head hurriedly. “Nein, I don’t think it’s dumb at all. Actually, I think it’s a wonderful idea.”

“Really?” Jester asked.

He nodded. “Ja, I’d love that.”

“Oh man, Caleb, I’m going to give you the best tattoo ever.”


End file.
